Thanks for everyones input and the links posted. Its good to bounce different ideas off everyones head. You all offer good perspectives and opinions which I value.

After some hunting and pricing on a six speed trans swap I've decided for now to stick with the 5 speed manual and see how I like it. The cost involved doesn't make sense. I could step into an '04 and newer which I might just do. (3-4 grand on the high end to do the swap) I'm still crunching numbers and I have an independent dealer looking for me at auctions. He keeps tempting me with some nice 4.4's and I love the V8 power. But a lot of these at my target initial price range have just over 100k miles and the auto trans at that mileage could be iffy, but I guess its hit and miss with these to be fair. Let me know what you think.